Synthesis and biological activity of 9-mercaptodethiobiotin—a putative biotin precursor in Escherichia coli

Abstract

A total synthesis of (±)-9-mercaptodethiobiotin 3via the aldehyde 9 is described. Compound (±)-3 does not function as a biotin replacement factor for an E. coli mutant (SA291) lacking the entire biotin synthesis operon (bioABFCD^–) but supports growth of an E. coli bioA mutant. Compound (±)-3 also supports growth of transformed cells of SA291 carrying a plasmid encoding the E. coli biotin synthase (bioB) gene indicating that the compound may be able to substitute for dethiobiotin 2 as a substrate for biotin synthase.